Complementary Synthetic Approaches
to Constitutionally Diverse N-Aminoalkylated Isoindolinones: Application
to the Synthesis of Falipamil and 5-HT1A Receptor Ligand
Analogues

Magali Lorion; Axel Couture; Eric Deniau; Pierre Grandclaudon

doi:10.1055/s-0028-1088048

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Synthesis 2009(11): 1897-1903
DOI: 10.1055/s-0028-1088048

PAPER

Complementary Synthetic Approaches to Constitutionally Diverse N-Aminoalkylated Isoindolinones: Application to the Synthesis of Falipamil and 5-HT_1A Receptor Ligand Analogues

Magali Lorion^a,b, Axel Couture*^a,b, Eric Deniau^a,b, Pierre Grandclaudon^a,b
^a LCOP, Université des Sciences et Technologies de Lille 1, Bâtiment C3(2), 59655 Villeneuve d’Ascq, France
Fax: +33(3)20336309; e-Mail: axel.couture@univ-lille1.fr;
^b CNRS, UMR 8009 ‘Chimie Organique et Macromoléculaire’, 59655 Villeneuve d’Ascq, France

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Publikationsverlauf

Received 21 January 2009
Publikationsdatum:
14. April 2009 (online)

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Abstract

Different synthetic approaches for the elaboration of poly and diversely substituted isoindolinones tailed with constitutionally diverse aminoalkylated chains have been developed. The key step is based upon the preliminary assembly of the isoindolinone template equipped with hydroxyalkyl appendages. Subsequent manipulation of the terminal hydroxy functionality afforded the targeted compounds and the synthetic utility of these approaches has been emphasized by the synthesis of the bradycardic agent falipamil and 5-HT_1A receptor ligand analogues.

Key words

carbanions - metalation - lactams - ring closure - ring opening

References

1a Zhao XZ. Semenova EA. Vu BC. Maddali K. Marchand C. Hughes SH. Pommier Y. Burke TR. J. Med. Chem. 2008, 51: 251

Reference Ris Wihthout Link

Suche in Google Scholar
1b Maugeri C. Alisi MA. Apicella C. Cellai L. Dragone P. Fioravanzo E. Florio S. Furlotti G. Mangano G. Ombrato R. Luisi R. Pompei R. Rincicotti V. Russo V. Vitiello M. Cazzolla N. Bioorg. Med. Chem. 2008, 16: 3091

Reference Ris Wihthout Link

Suche in Google Scholar
1c Govindachari TR. Ravindranath KR. Viswanathan N. J. Chem. Soc., Perkin Trans. 1 1974, 1215

Reference Ris Wihthout Link
1d Pendrak I. Barney S. Wittrock R. Lambert DM. Kingsbury WD. J. Org. Chem. 1994, 59: 2623

Reference Ris Wihthout Link

Suche in Google Scholar
1e Yeo H. Li Y. Fu L. Zhu J.-L. Gullen EA. Dutschman GE. Lee Y. Chung R. Huang E.-S. Austin DJ. Cheng Y.-C. J. Med. Chem. 2005, 48: 534

Reference Ris Wihthout Link

Suche in Google Scholar
2a Taylor EC. Zhou P. Jennings LD. Mao Z. Hu B. Jun J.-G. Tetrahedron Lett. 1997, 38: 521

Reference Ris Wihthout Link

Suche in Google Scholar
2b Fuska J. Fuskova A. Proksa B. Zb. Pr. Chemickotechnol Fak, SVST 1979-1981 (pub. 1986), 285 ; Chem. Abstr. 1987, 106, 95582

Reference Ris Wihthout Link
3a Zeldis JB. inventors; PCT Int. Appl. WO 043378, . ; Chem. Abstr. 2004, 140, 417925

Reference Ris Wihthout Link
3b Hardcastle IR. Ahmed SU. Atkins H. Calvert AH. Curtin NJ. Farnie G. Golding BT. Griffin RJ. Guyenne S. Hutton C. Källblad P. Kemp SJ. Kitching MS. Newell DR. Norbedo S. Northen JS. Reid RJ. Saravanan K. Willems HMG. Lunec J. Bioorg. Med. Chem. Lett. 2005, 15: 1515

Reference Ris Wihthout Link

Suche in Google Scholar
3c Shinji C. Maeda S. Imai K. Yoshida M. Hashimoto Y. Miyachi H. Bioorg. Med. Chem. 2006, 14: 7625

Reference Ris Wihthout Link

Suche in Google Scholar
4a Linden M. Hadler D. Hofmann S. Hum. Psychopharmacol. 1997, 12: 445

Reference Ris Wihthout Link

Suche in Google Scholar
4b Zhuang Z.-P. Kung M.-P. Mu M. Kung HF. J. Med. Chem. 1998, 41: 157

Reference Ris Wihthout Link

Suche in Google Scholar
4c Norman MH. Minick DJ. Rigdon GC. J. Med. Chem. 1996, 39: 149

Reference Ris Wihthout Link

Suche in Google Scholar
5 Lippmann W. inventors; US Patent 4 267 189, . ; Chem. Abstr. 1981, 95, 61988

Reference Ris Wihthout Link
6 Lee HJ. Lim SJ. Oh SJ. Moon DH. Kim DJ. Tae J. Yoo KH. Bioorg. Med. Chem. Lett. 2008, 18: 1628

Reference Link Ris
Crossref Suche in Google Scholar
7a Hamprecht D. Micheli F. Tedesco G. Checchia A. Donati D. Petrone M. Terreni S. Wood M. Bioorg. Med. Chem. Lett. 2007, 17: 428

Reference Ris Wihthout Link

Suche in Google Scholar
7b Cappelli A. Anzini M. Vomero S. Mennuni L. Makovec F. Doucet E. Hamon M. Menziani MC. De Benedetti PG. Giorgi G. Ghelardini C. Collina S. Bioorg. Med. Chem. 2002, 10: 779

Reference Ris Wihthout Link

Suche in Google Scholar
8 Shinozuka T. Yamamoto Y. Hasegawa T. Saito K. Naito S. Tetrahedron Lett. 2008, 49: 1619

Reference Link Ris
Crossref Suche in Google Scholar
9 Reiffen M. Eberlein W. Mueller P. Psiorz M. Noll K. Heider J. Lillie C. Kobinger W. Luger P. J. Med. Chem. 1990, 33: 1496

Reference Link Ris
Crossref Suche in Google Scholar
10a Dai-Ho G. Mariano PS. J. Org. Chem. 1987, 52: 704

Reference Ris Wihthout Link

Suche in Google Scholar
10b Lorion M. Couture A. Deniau E. Grandclaudon P. Synthesis 2008, 2141

Reference Ris Wihthout Link
11 Sarabu R. Cooper JP. Cook CM. Cook CM. Gillespie P. Perrotta AV. Olson GL. Drug Des. Discov. 1998, 15: 191

Reference Link Ris
Suche in Google Scholar
12 Lillie C. Kobinger W. J. Cardiovasc. Pharmacol. 1983, 5: 1048

Reference Link Ris
Crossref Suche in Google Scholar
13a Brachmann J. Senges J. Hammann HD. Anders G. Beck L. Braun W. Kubler W. Z. Kardiol. 1979, 68: 635

Reference Ris Wihthout Link

Suche in Google Scholar
13b Daemmgen JW. Kadatz R. Diederen W. Arzneim.-Forsch. (Drug Res.) 1981, 31: 666

Reference Ris Wihthout Link

Suche in Google Scholar
14a Gross GJ. Daemmgen JW. J. Cardiovasc. Pharmacol. 1987, 10: 123

Reference Ris Wihthout Link

Suche in Google Scholar
14b Diederen W. van Meel JCA. J. Mol. Cell. Cardiol. 1986, 18 (Suppl. 2): 16

Reference Ris Wihthout Link

Suche in Google Scholar
14c Trach V. Daemmgen JW. J. Mol. Cell. Cardiol. 1986, 18 (Suppl. 2): 20

Reference Ris Wihthout Link

Suche in Google Scholar
14d Gross GJ. Daemmgen JW. J. Pharmacol. Exp. Ther. 1986, 238: 422

Reference Ris Wihthout Link

Suche in Google Scholar
14e Wenger HC. Siegl PKS. J. Cardiovasc. Pharmacol. 1987, 9: 246

Reference Ris Wihthout Link

Suche in Google Scholar
14f Siegl PKS. Morgan G. Can. J. Physiol. Pharmacol. 1987, 65: 146

Reference Ris Wihthout Link

Suche in Google Scholar
14g Siegl PKS. Wenger HC. Sweet CS. J. Cardiovasc. Pharmacol. 1984, 6: 565

Reference Ris Wihthout Link

Suche in Google Scholar
15a Levy S. Metge M. Hilaire J. Cointe R. Bru P. Eychenne JL. Grerard R. Eur. Heart J. 1987, 8: 1236

Reference Ris Wihthout Link

Suche in Google Scholar
15b Tryba M. Zenz M. Arzneim.-Forsch. (Drug Res.) 1987, 37: 1298

Reference Ris Wihthout Link

Suche in Google Scholar
15c Jost S. Schulz W. Kober G. Arzneim.-Forsch. (Drug Res.) 1985, 35 (II): 1279

Reference Ris Wihthout Link

Suche in Google Scholar
15d Herzog H. Simon H. Herz-Kreislauf 1983, 7: 354

Reference Ris Wihthout Link

Suche in Google Scholar
15e Gulker H. Eur. Heart J. 1987, 8 (Suppl. L): 141

Reference Ris Wihthout Link

Suche in Google Scholar
15f Gilfrich HJ. Oberhoffer M. Witzke J. Eur. Heart J. 1987, 8 (Suppl. L): 147

Reference Ris Wihthout Link

Suche in Google Scholar
15g Hilaire J. Broustet JP. Colle JP. Theron M. Br. J. Clin. Pharmacol. 1983, 16: 627

Reference Ris Wihthout Link

Suche in Google Scholar
16 Siegl PKS. Morgan G. Can. J. Physiol. Pharmacol. 1987, 65: 146

Reference Link Ris
Crossref Suche in Google Scholar
17 Nakasaki M. Yamagami K. Isoe S. Bull. Chem. Soc. Jpn. 1961, 34: 1189

Reference Link Ris
Crossref Suche in Google Scholar
18 Lipshutz BH. Liu Z.-P. Kayser F. Tetrahedron Lett. 1994, 35: 5567

Reference Link Ris
Crossref Suche in Google Scholar
19 Dai-Ho G. Mariano PS. J. Org. Chem. 1987, 52: 704

Reference Link Ris
Crossref Suche in Google Scholar
20 Chauncey DM. Andrews LJ. Keefer RM. J. Am. Chem. Soc. 1974, 96: 1850

Reference Link Ris
Crossref Suche in Google Scholar
21 Olivera R. SanMartin R. Dominguez E. Solans X. Urtiaga MK. Arriortua MI. J. Org. Chem. 2000, 65: 6398

Reference Link Ris
Crossref Suche in Google Scholar
22 Markaryan EA. Markaryan RE. Arustamyan ZS. Airepetyan GK. Sukasyan RS. Markaryan KZ. Asatryan TO. Pharm. Chem. J. 1997, 31: 13

Reference Link Ris
Suche in Google Scholar
23 Lu Y. Taylor RT. Heterocycles 2004, 62: 869

Reference Link Ris
Crossref Suche in Google Scholar
24 Murata K. Bull. Chem. Soc. Jpn. 1973, 46: 1752

Reference Link Ris
Crossref Suche in Google Scholar

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Complementary Synthetic Approaches to Constitutionally Diverse N-Aminoalkylated Isoindolinones: Application to the Synthesis of Falipamil and 5-HT_1A Receptor Ligand Analogues

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Abstract

Key words

References

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Complementary Synthetic Approaches to Constitutionally Diverse N-Aminoalkylated Isoindolinones: Application to the Synthesis of Falipamil and 5-HT1A Receptor Ligand Analogues

Publikationsverlauf

Abstract

Key words

References

Complementary Synthetic Approaches to Constitutionally Diverse N-Aminoalkylated Isoindolinones: Application to the Synthesis of Falipamil and 5-HT_1A Receptor Ligand Analogues